The game is rife with complex and unknowable aspects that can have a big impact on a player. I don't know how anyone can make serious progress or be successful without being part of a strong clan that they hang out with in TS or Discord. How many times have I heard a newer player ask an innocent question and then get a five minute education from someone, or multiple people, about all the aspects of that thing and all the implications and twists?
I don't think handholding is the answer and I wouldn't expect the devs to program in more tutorials or new interfaces at this point in the development cycle, but maybe some pop-up tips or hover-over texts would be helpful. I'd imagine this community could come up with a big list of these types of tips and identify where and when to show them.
A simple example might be, when you enter a battle with a ship in fleet, pop up a message that says 'Stay close to your fleet to maximize firepower!'. That little tip would be the answer to hundreds of posts about how completely useless fleet ships are when you are attacked, they'd just be mostly useless then

The problem is the logic around ROE, the difference in time passage and distances traveled in battle vs. OW assume only a single battle will occur.
When ships enter a battle instance they decouple from the OW and the passage of time is disconnected. You can 'travel' for 90 minutes in a battle instance and return to the OW in the same place you started. Meanwhile people outside the instance can cover vast distances in the same 90 minutes.
Once a battle ends and ships escape to the OW the logic of it all falls apart and the subsequent battles logically don't make sense. The resulting 'unfairness' of the situation discourages people from playing.

This is amazing!
What timezone are these published in? It's showing three PBs during my Friday evening but I'm US Pacific time and nothing cool ever happens in my evenings, so I'm guessing this is server time?

A wipe is at best, a temporary thing. It will be neato for a few days, maybe two weeks tops and then whatever balance issues are present in the current version of the game will resurface and stay there. The game would be best balanced for the long term by dealing with the issues as they are present in a mixed playerbase.
Starting over would be fun, but as has been mentioned you can do it at any time through self-service character re-creation if you want to.
I could probably tolerate anything except losing the wicked grind ship upgrade slots, good lord don't make me do the ones I already have over again.

What are the gameplay mechanics associated with dubloons? Why exactly do we have them in addition to reals?
If the intent is for them to stabilize at some value relative to reals and (maybe) easily be exchanged back and forth between the two, what is the purpose of the dubloon? Is there some super cool, interesting, or game enhancing aspect to them that I'm missing or failing to understand?
Earlier interactions with PVP marks and conquest marks kind of made sense to me. They were like this special currency you only got for doing differentiated activities. Almost like a simple reputation system. Dubloons I'm not really understanding.

I don't know if it's particularly smart but if you constantly turn back and forth, running parallel to the wind in each direction, keeping close to the AI eventually their firepower will overwhelm a single attacking ship of almost any type. The key is staying as close to the AI as possible, they won't stay close to you if you run in any one direction for any amount of time.
You have to drastically change your tactics to accommodate the limitations of the AI in a PVP fight in order to get any benefit from them. If you sail as if it was a 1v1 fight that just happens to have some AI in the battle instance you will certainly lose.

I always assume all forum conversations comparing ships are about [ELITE SHIP CAPTAIN WHO NEVER MAKES MISTAKES] vs. another [ELITE SHIP CAPTAIN WHO NEVER MAKES MISTAKES] and not about the infinite realm of possibility. Personally, I have sunk a Le Requin with a store bought Snow and it didn't even seem all that hard to me but at that point I hadn't read any of these threads that would have told me how impossible it would be.

RE: #4 - It feels like at this point there's a weird mix of "let's be historically accurate" and "let's balance the game for playability" in the ships and their specs. Having great game play requires ahistorical balancing of ship specs. Adjusting the various rates and choices within the rates to a rock/paper/scissors setup would probably help the game a lot.
This would also help ensure that every ship in the game would have some advantage or reason to be used. The devs have consistently said that ships and combat are the main content of this game and everything else is just window dressing or the board upon which the ships/combat play. If this is the case, why not balance the ship specs so that all the content is viable?

There are bunch of one on ones like this I haven't jumped into because I'm thinking that there is some sort of trickery where what I thought was going to be a 1x1 ends up being a 6x1 because of others hiding in another battle, or some shenanigans around timers and whatnot. I know there have been a lot of small changes and tweaks, is such nonsense still possible or is a open world tag truly what-you-see-is-what-you-get now?

The devs have said over and over again the ships are the content, that's why they want you to grind through them all in a linear fashion.
That said I do have a problem with grinding up a ship to something usable and then going to the next ship up the ladder and being less effective (I'm looking at you starting Snow with your 4lb cannons).

Wouldn't I be better able to wage war if a ship I dealt massive damage to couldn't fully repair and re-crew in a few moments without visiting a port? If you want to make the game more fluid how about just give me my ship back after I'm sunk in battle and have me reappear in the same spot in the open world ready to fight again?